n-Dodecyl­ammonium bromide monohydrate

Dan, W.; Di, Y.; He, D.; Yang, W.; Kong, Y.

doi:10.1107/S1600536810010123

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o910

doi:10.1107/S1600536810010123

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n-Dodecylammonium bromide monohydrate

Wenyan Dan,^a Youying Di,^a ^* Donghua He,^a Weiwei Yang ^a and Yuxia Kong ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: diyouying@126.com

(Received 14 March 2010; accepted 18 March 2010; online 24 March 2010)

In the title compound, C₁₂H₂₈N⁺·Br⁻·H₂O, the ionic pairs formed by n-dodecylammonium cations and bromide anions are arranged into thick layers; these layers are linked in a nearly perpendicular fashion [the angle between the layers is 85.84 (5)°] by hydrogen-bonding interactions involving the water molecules. The methylene part of the alkyl chain in the cation adopts an all-trans conformation. In the crystal structure, molecules are linked by intermolecular N—H⋯Br, O—H⋯Br and N—H⋯O hydrogen bonds.

Related literature

Long-chain n-alkylammonium halides are widely used as surfactants (Aratono et al., 1998 ; Tornblom et al., 2000 ) and as models for biological membranes (Ringsdorf et al., 1988 ). They exhibit polymorphism at room temperature: for solid-solid phase transitions in n–alkylammonium chlorides, see: Terreros et al. (2000 ). For a related structure, see: Lundén (1974 ).

Experimental

Crystal data

C₁₂H₂₈N⁺·Br⁻·H₂O
M_r = 284.28
Monoclinic, C c
a = 4.7921 (5) Å
b = 42.810 (4) Å
c = 7.8573 (8) Å
β = 105.798 (2)°
V = 1551.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.63 mm⁻¹
T = 293 K
0.42 × 0.14 × 0.06 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.404, T_max = 0.858
4760 measured reflections
2644 independent reflections
1665 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.081
S = 0.92
2644 reflections
145 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 945 Friedel pairs
Flack parameter: 0.048 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1ⁱ	0.89	2.53	3.380 (4)	159
N1—H1B⋯Br1	0.89	2.47	3.340 (4)	166
N1—H1C⋯O1	0.89	1.97	2.834 (7)	165
O1—H1⋯Br1ⁱⁱ	0.83 (4)	2.76 (6)	3.329 (5)	128 (6)
O1—H2⋯Br1ⁱⁱⁱ	0.97 (4)	2.49 (5)	3.361 (5)	149 (5)
Symmetry codes: (i) $[x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x+1, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010123/lx2141sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010123/lx2141Isup2.hkl

checkCIF report

Comment top

Long-chain n-alkylammonium halides are widely used as surfactants (Aratono et al., 1998; Tornblom et al., 2000) and as models for biological membranes (Ringsdorf et al., 1988). They exhibit polymorphism at room temperature; solid-solid phase transitions occurred in n-alkylammonium chlorides (Terreros et al., 2000). As a part of the studies on novel potential phase transfer materials with the thermochemical properties such as n-alkylammonium chlorides, we report the crystal structure of the title compound (Fig. 1).

Atoms C3–C12 are coplanar in the title compound; however, atoms C2–C12 are coplanar in n–dodecylammonium bromide (Ludén, 1974). Although the methylene chain had the extended all–trans conformation, it is slightly curved in the vicinity of the ammonium group, to accommodate the hydrogen–bonding interactions. The hydrogen bonds of n–dodecylammonium bromide monohydrate are more stronger than that of n–dodecylammonium bromide because of N—H···O and O—H···Br hydrogen bonds. Only torsion angle C1–C2–C3–C4 deviates significantly from 180 °, with a value of 170.6 (5)°. The crystal packing (Fig. 2) is stabilized by intermolecular N—H···Br, N—H···O and O—H···Br hydrogen bonds (Table 1).

Related literature top

Long-chain n-alkylammonium halides are widely used as surfactants (Aratono et al., 1998; Tornblom et al., 2000) and as models for biological membranes (Ringsdorf et al., 1988). They exhibit polymorphism at room temperature: for solid-solid phase transitions in n–alkylammonium chlorides, see: Terreros et al. (2000). For a related structure, see: Lundén (1974).

Experimental top

n–Dodecylammonium bromide monohydrate was prepared by the addition of hydrobromic acid to an ethanol solution of n–dodecylamine. The resulting precipitate was filtered off and recrystallized several times from chloroform. Single crystals suitable for X–ray diffraction were prepared by evaporation of a solution of the title compound in chloroform at room temperature. Analysis, calculated for C₁₂H₃₀BrNO (Mr = 284.28): C 50.69, H 10.64, N 4.93, O 5.63, Br 28.11%; found: C 50.67, H 10.65, N 4.91, O 5.64, Br 28.13%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. N—H···Br, N—H···O and O—H···Br interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x + 1, - y + 1, z + 1/2; (ii) x, - y +1 , z - 1/2; (iii) x + 1, - y + 1, z - 1/2]

n-Dodecylammonium bromide monohydrate top

Crystal data top

C₁₂H₂₈N⁺·Br⁻·H₂O	F(000) = 608
M_r = 284.28	D_x = 1.217 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1266 reflections
a = 4.7921 (5) Å	θ = 2.9–25.0°
b = 42.810 (4) Å	µ = 2.63 mm⁻¹
c = 7.8573 (8) Å	T = 293 K
β = 105.798 (2)°	Acicular, colourless
V = 1551.0 (3) Å³	0.42 × 0.14 × 0.06 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2644 independent reflections
Radiation source: fine-focus sealed tube	1665 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 10 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ϕ and ω scans	h = −6→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −54→50
T_min = 0.404, T_max = 0.858	l = −6→10
4760 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0277P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
2644 reflections	Δρ_max = 0.40 e Å⁻³
145 parameters	Δρ_min = −0.24 e Å⁻³
5 restraints	Absolute structure: Flack (1983), 945 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.048 (19)

Crystal data top

C₁₂H₂₈N⁺·Br⁻·H₂O	V = 1551.0 (3) Å³
M_r = 284.28	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 4.7921 (5) Å	µ = 2.63 mm⁻¹
b = 42.810 (4) Å	T = 293 K
c = 7.8573 (8) Å	0.42 × 0.14 × 0.06 mm
β = 105.798 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2644 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1665 reflections with I > 2σ(I)
T_min = 0.404, T_max = 0.858	R_int = 0.047
4760 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	Δρ_max = 0.40 e Å⁻³
S = 0.92	Δρ_min = −0.24 e Å⁻³
2644 reflections	Absolute structure: Flack (1983), 945 Friedel pairs
145 parameters	Absolute structure parameter: 0.048 (19)
5 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.2086 (2)	0.524590 (10)	0.38293 (16)	0.05643 (18)
O1	0.8268 (12)	0.45062 (13)	0.1580 (6)	0.0760 (15)
H1	0.734 (13)	0.4485 (18)	0.053 (6)	0.114*
H2	0.993 (11)	0.4589 (15)	0.124 (9)	0.114*
N1	0.7249 (9)	0.46990 (8)	0.4809 (6)	0.0502 (12)
H1A	0.8831	0.4731	0.5697	0.075*
H1B	0.6083	0.4864	0.4696	0.075*
H1C	0.7755	0.4671	0.3810	0.075*
C1	0.5729 (12)	0.44200 (13)	0.5176 (8)	0.0496 (17)
H1D	0.3952	0.4392	0.4238	0.059*
H1E	0.5212	0.4449	0.6276	0.059*
C2	0.7567 (11)	0.41323 (10)	0.5313 (7)	0.0480 (14)
H2A	0.9345	0.4161	0.6249	0.058*
H2B	0.8084	0.4104	0.4213	0.058*
C3	0.6028 (11)	0.38403 (11)	0.5696 (7)	0.0496 (14)
H3A	0.5795	0.3855	0.6881	0.059*
H3B	0.4108	0.3831	0.4875	0.059*
C4	0.7635 (11)	0.35416 (10)	0.5545 (7)	0.0466 (14)
H4A	0.7908	0.3531	0.4367	0.056*
H4B	0.9540	0.3550	0.6382	0.056*
C5	0.6137 (11)	0.32477 (11)	0.5877 (7)	0.0484 (14)
H5A	0.5955	0.3254	0.7076	0.058*
H5B	0.4194	0.3245	0.5082	0.058*
C6	0.7625 (11)	0.29500 (11)	0.5641 (7)	0.0488 (14)
H6A	0.9550	0.2951	0.6458	0.059*
H6B	0.7859	0.2947	0.4453	0.059*
C7	0.6105 (11)	0.26515 (11)	0.5920 (7)	0.0454 (13)
H7A	0.5909	0.2651	0.7117	0.055*
H7B	0.4168	0.2651	0.5117	0.055*
C8	0.7621 (11)	0.23602 (11)	0.5640 (7)	0.0484 (14)
H8A	0.9555	0.2361	0.6447	0.058*
H8B	0.7827	0.2362	0.4446	0.058*
C9	0.6128 (11)	0.20610 (11)	0.5905 (7)	0.0495 (14)
H9A	0.4180	0.2062	0.5116	0.059*
H9B	0.5957	0.2058	0.7107	0.059*
C10	0.7642 (12)	0.17604 (11)	0.5585 (7)	0.0508 (14)
H10A	0.7842	0.1766	0.4389	0.061*
H10B	0.9579	0.1757	0.6387	0.061*
C11	0.6143 (13)	0.14651 (12)	0.5818 (8)	0.0592 (16)
H11A	0.5946	0.1459	0.7014	0.071*
H11B	0.4205	0.1468	0.5016	0.071*
C12	0.7623 (15)	0.11758 (13)	0.5502 (9)	0.080 (2)
H12A	0.7850	0.1179	0.4325	0.121*
H12B	0.6483	0.0998	0.5634	0.121*
H12C	0.9496	0.1163	0.6342	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0519 (3)	0.0577 (3)	0.0587 (3)	0.0057 (6)	0.0134 (2)	0.0063 (5)
O1	0.078 (3)	0.085 (4)	0.069 (3)	0.006 (3)	0.025 (3)	0.006 (3)
N1	0.051 (3)	0.038 (3)	0.056 (3)	0.006 (2)	0.005 (2)	0.0026 (19)
C1	0.050 (4)	0.032 (3)	0.067 (5)	0.001 (3)	0.017 (3)	0.004 (3)
C2	0.052 (3)	0.036 (3)	0.057 (4)	−0.001 (3)	0.016 (3)	0.000 (2)
C3	0.053 (4)	0.043 (3)	0.059 (4)	0.001 (3)	0.027 (3)	0.007 (3)
C4	0.047 (3)	0.039 (3)	0.056 (4)	0.000 (3)	0.017 (3)	0.001 (3)
C5	0.057 (4)	0.041 (3)	0.052 (3)	0.001 (3)	0.024 (3)	−0.005 (3)
C6	0.053 (3)	0.044 (3)	0.049 (3)	−0.003 (3)	0.013 (3)	0.000 (3)
C7	0.048 (3)	0.036 (3)	0.056 (3)	−0.001 (3)	0.020 (3)	0.001 (3)
C8	0.050 (3)	0.042 (3)	0.055 (3)	−0.003 (3)	0.017 (3)	−0.001 (3)
C9	0.051 (4)	0.046 (3)	0.056 (4)	−0.007 (3)	0.021 (3)	−0.001 (3)
C10	0.058 (4)	0.048 (3)	0.047 (3)	0.000 (3)	0.015 (3)	0.001 (3)
C11	0.073 (4)	0.041 (3)	0.067 (4)	−0.011 (3)	0.026 (3)	−0.001 (3)
C12	0.104 (5)	0.041 (4)	0.097 (5)	0.003 (4)	0.028 (4)	−0.007 (3)

Geometric parameters (Å, º) top

O1—H1	0.83 (4)	C6—C7	1.516 (6)
O1—H2	0.97 (4)	C6—H6A	0.9700
N1—C1	1.468 (7)	C6—H6B	0.9700
N1—H1A	0.8900	C7—C8	1.490 (6)
N1—H1B	0.8900	C7—H7A	0.9700
N1—H1C	0.8900	C7—H7B	0.9700
C1—C2	1.501 (7)	C8—C9	1.509 (7)
C1—H1D	0.9700	C8—H8A	0.9700
C1—H1E	0.9700	C8—H8B	0.9700
C2—C3	1.522 (6)	C9—C10	1.532 (7)
C2—H2A	0.9700	C9—H9A	0.9700
C2—H2B	0.9700	C9—H9B	0.9700
C3—C4	1.514 (7)	C10—C11	1.490 (7)
C3—H3A	0.9700	C10—H10A	0.9700
C3—H3B	0.9700	C10—H10B	0.9700
C4—C5	1.506 (6)	C11—C12	1.481 (8)
C4—H4A	0.9700	C11—H11A	0.9700
C4—H4B	0.9700	C11—H11B	0.9700
C5—C6	1.496 (6)	C12—H12A	0.9600
C5—H5A	0.9700	C12—H12B	0.9600
C5—H5B	0.9700	C12—H12C	0.9600

H1—O1—H2	91 (5)	C5—C6—H6B	108.3
C1—N1—H1A	109.5	C7—C6—H6B	108.3
C1—N1—H1B	109.5	H6A—C6—H6B	107.4
H1A—N1—H1B	109.5	C8—C7—C6	114.3 (4)
C1—N1—H1C	109.5	C8—C7—H7A	108.7
H1A—N1—H1C	109.5	C6—C7—H7A	108.7
H1B—N1—H1C	109.5	C8—C7—H7B	108.7
N1—C1—C2	111.6 (5)	C6—C7—H7B	108.7
N1—C1—H1D	109.3	H7A—C7—H7B	107.6
C2—C1—H1D	109.3	C7—C8—C9	114.9 (4)
N1—C1—H1E	109.3	C7—C8—H8A	108.5
C2—C1—H1E	109.3	C9—C8—H8A	108.5
H1D—C1—H1E	108.0	C7—C8—H8B	108.5
C1—C2—C3	112.4 (4)	C9—C8—H8B	108.5
C1—C2—H2A	109.1	H8A—C8—H8B	107.5
C3—C2—H2A	109.1	C8—C9—C10	115.3 (4)
C1—C2—H2B	109.1	C8—C9—H9A	108.5
C3—C2—H2B	109.1	C10—C9—H9A	108.5
H2A—C2—H2B	107.9	C8—C9—H9B	108.5
C4—C3—C2	113.2 (4)	C10—C9—H9B	108.5
C4—C3—H3A	108.9	H9A—C9—H9B	107.5
C2—C3—H3A	108.9	C11—C10—C9	115.3 (4)
C4—C3—H3B	108.9	C11—C10—H10A	108.5
C2—C3—H3B	108.9	C9—C10—H10A	108.5
H3A—C3—H3B	107.8	C11—C10—H10B	108.5
C5—C4—C3	114.6 (4)	C9—C10—H10B	108.5
C5—C4—H4A	108.6	H10A—C10—H10B	107.5
C3—C4—H4A	108.6	C12—C11—C10	114.8 (5)
C5—C4—H4B	108.6	C12—C11—H11A	108.6
C3—C4—H4B	108.6	C10—C11—H11A	108.6
H4A—C4—H4B	107.6	C12—C11—H11B	108.6
C6—C5—C4	115.1 (4)	C10—C11—H11B	108.6
C6—C5—H5A	108.5	H11A—C11—H11B	107.5
C4—C5—H5A	108.5	C11—C12—H12A	109.5
C6—C5—H5B	108.5	C11—C12—H12B	109.5
C4—C5—H5B	108.5	H12A—C12—H12B	109.5
H5A—C5—H5B	107.5	C11—C12—H12C	109.5
C5—C6—C7	115.9 (4)	H12A—C12—H12C	109.5
C5—C6—H6A	108.3	H12B—C12—H12C	109.5
C7—C6—H6A	108.3

N1—C1—C2—C3	179.9 (4)	C5—C6—C7—C8	178.9 (4)
C1—C2—C3—C4	170.6 (5)	C6—C7—C8—C9	−179.7 (5)
C2—C3—C4—C5	−178.7 (4)	C7—C8—C9—C10	178.9 (4)
C3—C4—C5—C6	177.0 (5)	C8—C9—C10—C11	−179.1 (5)
C4—C5—C6—C7	−178.4 (4)	C9—C10—C11—C12	179.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1ⁱ	0.89	2.53	3.380 (4)	159
N1—H1B···Br1	0.89	2.47	3.340 (4)	166
N1—H1C···O1	0.89	1.97	2.834 (7)	165
O1—H1···Br1ⁱⁱ	0.83 (4)	2.76 (6)	3.329 (5)	128 (6)
O1—H2···Br1ⁱⁱⁱ	0.97 (4)	2.49 (5)	3.361 (5)	149 (5)

Symmetry codes: (i) x+1, −y+1, z+1/2; (ii) x, −y+1, z−1/2; (iii) x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₂₈N⁺·Br⁻·H₂O
M_r	284.28
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	4.7921 (5), 42.810 (4), 7.8573 (8)
β (°)	105.798 (2)
V (Å³)	1551.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.63
Crystal size (mm)	0.42 × 0.14 × 0.06

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.404, 0.858
No. of measured, independent and observed [I > 2σ(I)] reflections	4760, 2644, 1665
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.081, 0.92
No. of reflections	2644
No. of parameters	145
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.24
Absolute structure	Flack (1983), 945 Friedel pairs
Absolute structure parameter	0.048 (19)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1ⁱ	0.89	2.53	3.380 (4)	159.4
N1—H1B···Br1	0.89	2.47	3.340 (4)	166.4
N1—H1C···O1	0.89	1.97	2.834 (7)	164.6
O1—H1···Br1ⁱⁱ	0.83 (4)	2.76 (6)	3.329 (5)	128 (6)
O1—H2···Br1ⁱⁱⁱ	0.97 (4)	2.49 (5)	3.361 (5)	149 (5)

Symmetry codes: (i) x+1, −y+1, z+1/2; (ii) x, −y+1, z−1/2; (iii) x+1, −y+1, z−1/2.

Acknowledgements

We acknowledge financial support by the National Natural Science Foundations of China (20673050 and 20973089).

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